Well I definitely don't want to hose my OS, the whole point of installing MonoDevelop in the first place was to continue to develop .NET applications, but under Linux (since I don't intend to continue using Windows beyond Windows 7, but I still need to develop for it). Since these are new installations of Linux Lite, I can redo them without too much impact. Would that be the recommended process? or is there a way to roll back from my current MonoDevelop installation and then install an older one from the default repositories.

Yeah the official Ubuntu 14.04 PPAs will let me install MonoDevelop v4.0, but it's a bit old. The current version is v5.9 and there have been many bug fixes and feature editions since v4.0. I could always attempt to build it from source (but that's another bag of worms). A friend recommended I search across LauchPad.net fist , and I found this PPA:

* Strangely enough, the repo listed above is listed as obsolete, and then points to the original instructions I followed that had me add the Debian PPAs to my system...

I guess the maintainer has other issues in life.

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Latest updates

mono-4 , 21 weeks ago Successfully built

Reminds me of Sis, Savage, Via, graphics driver maintainer also. Sadly, we are few and far between. I used to maintain pianobar for Puppy Linux users till I got burned out doing it every week trying to keep up with pandora breaking it on purpose.

but reading over that guide it states the .NET 5 Core team is using Ubuntu 14.04 LTS, so they're including Debian repos under Ubuntu as well... it seems like this is pretty much unavoidable if I want to keep to LTS, but develop using the latest tools. I mean I was able to get Visual Studio Code (their cross platform editor) installed and running without issue (it was just a zip). But now I'm at another road block.

If you don't get the issue from the command I supplied, but you do with the GUI, then the GUI runs a different command. I wouldn't recommend giving up on the GUI. It's doing what it's supposed to do. And in your case, it's letting us know something is odd. The GUI also more than likely produces a log even when you cancel out of the process. I just don't know where that log file is. Perhaps someone else will chime in.

Just as a heads up, it appears the GUI updater is a script run from /usr/scripts/updates-gui and it generates a log in /var/logs/llupdates.log. However I'm not sure if this file is generated line for line while the updates are running, or if it is only generated after the updates are done all in one shot. Just wanted to let you know, since I was able to track these down.